Hydrogen Peroxide → 2-benzyloxy-5-(2-hydroxyethyl)-N,N-dimethylbenzamide

To a stirred solution of 2-benzyloxy-N,N-dimethyl-5-vinylbenzamide (560 mg) in tetrahydrofuran (5 ml) was added dropwise a solution of 9-borabicyclo[3.3.1]nonane (255 mg) in tetrahydrofuran (8 ml) at −20° C. under an argon atmosphere, and the mixture was stirred for 14.5 hours at room temperature. To the stirred reaction mixture were added 2N aqueous sodium hydroxide solution (3.0 ml) and 30% aqueous hydrogen peroxide solution (2.4 ml) under ice-cooling, and the resulting mixture was stirred for 5 hours at room temperature. To the reaction mixture was added water, and the resulting mixture was extracted with dichloromethane. The extract was washed with brine and dried over anhydrous magnesium sulfate. After the solvent was removed under reduced pressure, purification of the residue by flash column chromatography on silica gel (eluent:hexane/diethyl ether/dichloromethane=1/2/2 and methanol/diethyl ether/dichloromethane=1/10/10) gave 2-benzyloxy-5-(2-hydroxyethyl)-N,N-dimethylbenzamide (300 mg).

1. customTo the stirred reaction mixture
2. temperaturecooling
3. stirringthe resulting mixture was stirred for 5 hours at room temperature
4. extractionthe resulting mixture was extracted with dichloromethane
5. washThe extract was washed with brine
6. dry with materialdried over anhydrous magnesium sulfate
7. customAfter the solvent was removed under reduced pressure, purification of the residue by flash column chromatography on silica gel (eluent:hexane/diethyl ether/dichloromethane=1/2/2 and methanol/diethyl ether/dichloromethane=1/10/10)

ORD-Eintrag

ord-5668962651294473a066b66bc1408cb1

Quelldatensatz

uspto-grants-2003_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06538152B1